CN115768758A - Novel compound and organic light emitting device comprising same - Google Patents
Novel compound and organic light emitting device comprising same Download PDFInfo
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- CN115768758A CN115768758A CN202180043938.XA CN202180043938A CN115768758A CN 115768758 A CN115768758 A CN 115768758A CN 202180043938 A CN202180043938 A CN 202180043938A CN 115768758 A CN115768758 A CN 115768758A
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- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
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Abstract
The invention provides a novel compound and an organic light emitting device using the same.
Description
Technical Field
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2020-0114079 on 9/7/2020 and includes the entire disclosure of the korean patent application as part of the present specification.
The present invention relates to a novel compound and an organic light emitting device comprising the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, a fast response time, and excellent luminance, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
An organic light emitting device generally has a structure including an anode and a cathode, and an organic layer between the anode and the cathode. In order to improve the efficiency and stability of the organic light emitting device, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons (exiton) are formed, which emit light when they transition to the ground state again.
Development of new materials is continuously required for organic materials used for the organic light emitting devices as described above.
Documents of the prior art
Patent document
(patent document 0001) Korean patent laid-open publication No. 10-2000-0051826
Disclosure of Invention
Technical subject
The present invention relates to a novel compound and an organic light emitting device comprising the same.
Means for solving the problems
The present invention provides a compound represented by the following chemical formula 1:
[ chemical formula 1]
In the above-mentioned chemical formula 1,
l, L' and L 1 To L 4 Each independently a single bond, or a substituted or unsubstituted C 6-60 An arylene group, a heterocyclic group, or a heterocyclic group,
Ar 1 to Ar 4 Each independently is substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C containing 1 or more heteroatoms of N, O and S 2-60 (ii) a heteroaryl group, wherein,
R 1 and R 2 Each independently hydrogen, deuterium, substituted or unsubstituted C 1-60 Alkyl, or substituted or unsubstituted C 6-60 An aryl group, a heteroaryl group,
n and m are each independently an integer of 0 to 2,
however, n + m is 1 to 3,
a is an integer of 0 to 4-m,
b is an integer of 0 to 6-n,
when n, m, a and b are each 2 or more, the substituents in parentheses may be the same or different from each other.
In addition, the present invention provides an organic light emitting device, comprising: the organic light emitting device includes a first electrode, a second electrode disposed to face the first electrode, and 1 or more organic layers disposed between the first electrode and the second electrode, wherein 1 or more of the organic layers include a compound represented by the chemical formula 1.
Effects of the invention
The compound represented by the above chemical formula 1 may be used as a material of an organic layer of an organic light emitting device in which improvement in efficiency, lower driving voltage, and/or improvement in lifetime characteristics may be achieved.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole transport layer 3, a light-emitting layer 4, an electron injection and transport layer 5, and a cathode 6.
Fig. 2 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, an electron suppression layer 8, a light-emitting layer 4, a hole blocking layer 9, an electron injection and transport layer 5, and a cathode 6.
Detailed Description
Hereinafter, the present invention will be described in more detail to assist understanding thereof.
(definition of wording)
In the context of the present specification,
and
represents a bond to other substituents.
In the present specification, the term "substituted or unsubstituted" means substituted with a substituent selected from deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; alkylthio radicals
Aryl sulfur radical
Alkyl sulfonyl radical
Aryl sulfonyl radical
A silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamino group; an aralkylamino group; a heteroaryl amino group; an arylamine group; aryl phosphinesA group; or 1 or more substituents of 1 or more heteroaryl groups containing N, O and S atoms, or substituents linked by 2 or more substituents of the above-exemplified substituents. For example, the "substituent in which 2 or more substituents are bonded" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the substituent may be a substituent having the following structure, but is not limited thereto.
In the present specification, in the ester group, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, the substituent may be a substituent represented by the following structural formula, but is not limited thereto.
In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the substituent may be a substituent having the following structure, but is not limited thereto.
In the present specification, specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.
In the present specification, the boron group specifically includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like, but is not limited thereto.
In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.
In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl.
In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the above alkenyl group is 2 to 6. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylethen-1-yl, 2-phenylethen-1-yl, 2,2-diphenylethen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2,2-bis (biphenyl-1-yl) ethen-1-yl, stilbene-yl, styryl and the like, but the present invention is not limited thereto.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, and according to one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 6. Specifically, there are mentioned, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, adamantyl, and the like.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aromatic group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a perylene group,
And a fluorenyl group, but is not limited thereto.
In the present specification, the fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. When the fluorenyl group is substituted, the compound may be
And the like. But is not limited thereto.
In the present specification, the heteroaryl group is a heteroaryl group containing 1 or more of O, N, si and S as a hetero element, and the number of carbon atoms is not particularly limited, but preferably 2 to 60. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, thienyl,
Azolyl group,
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl (phenanthroline), isoquinoyl
Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.
In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, arylamine group, and arylsilyl group is the same as the aryl group described above. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamino group is the same as the above-mentioned alkyl group. In the present specification, the heteroaryl group in the heteroarylamino group can be applied to the above description about the heteroaryl group. In the present specification, the alkenyl group in the aralkenyl group is exemplified by the same alkenyl groups as described above. In the present specification, the arylene group is a 2-valent group, and the above description of the aryl group can be applied thereto. In the present specification, a heteroarylene group is a 2-valent group, and in addition to this, the above description about a heteroaryl group can be applied. In the present specification, the hydrocarbon ring is not a 1-valent group but is formed by combining 2 substituents, and in addition to this, the above description about the aryl group or the cycloalkyl group can be applied. In the present specification, the heterocyclic ring is not a 1-valent group but is formed by combining 2 substituents, and in addition to this, the above description on the heteroaryl group can be applied.
(Compound (I))
In another aspect, the present invention provides a compound represented by the above chemical formula 1.
Specifically, the compound represented by the above chemical formula 1 is a compound in which an amino group is bonded to a benzene ring of a benzo [ b ] naphtho [1,8-ef ] [1,4] dioxepin (benzo [ b ] naphtho [1,8-ef ] [1,4] dioxepin) core, and has a characteristic that 1 or 2 amino groups can be selectively bonded to a naphthalene ring of the core.
The compound having such a structure exhibits improved hole transport ability and improved thermal stability due to the structure as described above, and thus an organic light emitting device using the compound can exhibit characteristics such as high efficiency, low driving voltage, and long life compared to conventional organic light emitting devices.
Specifically, the above compound may be represented by any one of the following chemical formulas 1A to 1C:
[ chemical formula 1A ]
[ chemical formula 1B ]
[ chemical formula 1C ]
In the above chemical formulas 1A to 1C,
L、L'、L 1 to L 4 、Ar 1 To Ar 4 、R 1 、R 2 N, m, a and b are the same as defined in the above chemical formula 1.
More specifically, the compound represented by the above chemical formula 1A may be represented by the following chemical formula 1A':
[ chemical formula 1A' ]
In the above chemical formula 1A',
L、L 1 、L 2 、Ar 1 、Ar 2 、R 1 and a is the same as defined in the above chemical formula 1,
may be Z 1 To Z 6 Each independently is R 2 (ii) a Or
Z 1 To Z 6 One of which is a substituent represented by the following chemical formula a, and the others are each independently R 2 (ii) a Or
Z 1 To Z 6 Two of which are each independently a substituent represented by the following chemical formula a, and the others are each independently R 2 ，
[ chemical formula a ]
In the chemical formula a described above,
L'、L 3 、L 4 、Ar 3 and Ar 4 The same as defined in the above chemical formula 1.
For example, in the above chemical formula 1A',
may be Z 1 To Z 6 Each independently is R 2 (ii) a Or
Z 1 Is a substituent represented by the above chemical formula a, Z 2 To Z 6 Each independently is R 2 (ii) a Or alternatively
Z 2 Is a substituent represented by the above chemical formula a, Z 1 And Z 3 To Z 6 Each independently is R 2 (ii) a Or
Z 3 Is a substituent represented by the above chemical formula a; z 1 、Z 2 And Z 4 To Z 6 Each independently is R 2 (ii) a Or
Z 4 Is a substituent represented by the above chemical formula a, Z 1 To Z 3 、Z 5 And Z 6 Each independently is R 2 (ii) a Or
Z 5 Is a substituent represented by the above chemical formula a, Z 1 To Z 4 And Z 6 Each independently is R 2 (ii) a Or
Z 6 Is a substituent represented by the above chemical formula a, Z 1 To Z 5 Each independently is R 2 。
In addition, the compound represented by the above chemical formula 1B may be represented by the following chemical formula 1B':
[ chemical formula 1B' ]
In the above chemical formula 1B',
L、L 1 、L 2 、Ar 1 、Ar 2 、R 1 and a is the same as defined in the above chemical formula 1,
may be Z 1 To Z 6 Each independently is R 2 (ii) a Or alternatively
Z 1 To Z 6 One of which is a substituent represented by the above formula a, and the others are each independently R 2 (ii) a Or
Z 1 To Z 6 Two of which are each independently a substituent represented by the above formula a, and the others are each independently R 2 。
For example, in the above chemical formula 1B',
may be Z 1 To Z 6 Each independently is R 2 (ii) a Or
Z 1 Is a substituent represented by the above chemical formula a, Z 2 To Z 6 Each independently is R 2 (ii) a Or
Z 2 Is a substituent represented by the above chemical formula a, Z 1 And Z 3 To Z 6 Each independently is R 2 (ii) a Or
Z 3 Is a substituent represented by the above chemical formula a, Z 1 、Z 2 And Z 4 To Z 6 Each of which isIndependently is R 2 (ii) a Or
Z 4 Is a substituent represented by the above chemical formula a, Z 1 To Z 3 、Z 5 And Z 6 Each independently is R 2 (ii) a Or
Z 5 Is a substituent represented by the above chemical formula a, Z 1 To Z 4 And Z 6 Each independently is R 2 (ii) a Or
Z 6 Is a substituent represented by the above chemical formula a, Z 1 To Z 5 Each independently is R 2 。
In addition, the compound represented by the above chemical formula 1C may be represented by the following chemical formula 1C':
[ chemical formula 1C' ]
In the above chemical formula 1C',
L'、L 3 、L 4 、Ar 3 、Ar 4 、R 2 and b is the same as defined in the above chemical formula 1,
may be Z 7 To Z 10 Each independently is R 1 (ii) a Or
Z 1 To Z 6 One of them is a substituent represented by the following chemical formula b, and the others are each independently R 1 (ii) a Or
Z 1 To Z 6 Two of which are each independently a substituent represented by the above chemical formula b, and the others are each independently R 1 ，
[ chemical formula b ]
In the chemical formula b described above,
L、L 1 、L 2 、Ar 1 、Ar 2 、R 1 and a is the same as that in the above chemical formula 1The definitions are the same.
For example, in the above chemical formula 1C',
may be Z 7 To Z 10 Each independently is R 1 (ii) a Or
Z 7 Is a substituent represented by the above chemical formula b, Z 8 To Z 10 Each independently is R 1 (ii) a Or
Z 8 Is a substituent represented by the above chemical formula b, Z 7 、Z 9 And Z 10 Each independently is R 1 (ii) a Or
Z 9 Is a substituent represented by the above chemical formula b, Z 7 、Z 8 And Z 10 Each independently is R 1 (ii) a Or
Z 10 Is a substituent represented by the above chemical formula b, Z 7 To Z 9 Each independently is R 1 。
In addition, in the above chemical formula 1, each of L and L' independently may be a single bond, or C unsubstituted or substituted with deuterium 6-20 An arylene group.
Specifically, L and L' may each independently be a single bond, phenylene, biphenyldiyl, or naphthylene.
More specifically, L and L' each independently may be a single bond, or selected from any one of the following groups:
for example, it may be that both L and L ' are single bonds, or both L and L ' are phenylene, or one of L and L ' is a single bond and the other is any one selected from the following groups:
in addition, in the above chemical formula 1, L 1 To L 4 Each independently may be a single bond, phenylene, biphenyldiyl or naphthyleneAnd (4) a base.
More specifically, L 1 To L 4 Each independently may be a single bond, or any one selected from the following groups:
for example, it may be L 1 And L 2 Are all single bonds, or L 1 And L 2 One is a single bond and the other is any one selected from the following groups:
further, for example, L may be 3 And L 4 Are all single bonds, or L 3 And L 4 One is a single bond and the other is any one selected from the following groups:
in addition, in the above chemical formula 1, ar 1 To Ar 4 Each independently is C 6-20 Aryl, dibenzofuranyl or dibenzothienyl,
here, ar is 1 To Ar 4 May be unsubstituted or may be selected from deuterium, C 1-10 Alkyl and C 6-20 And 1 or more substituents in the aryl group.
Specifically, ar 1 To Ar 4 Each independently of the others is phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, dibenzofuranyl or dibenzothiophenyl,
here, ar is 1 To Ar 4 May be unsubstituted or may be selected from deuterium, C 1-10 Alkyl and C 6-20 1 or more substituents in the aryl group, for example selected from deuterium, methyl, ethyl, propyl, isopropyl,1 or more substituents selected from the group consisting of butyl, tert-butyl and phenyl.
More specifically, ar 1 To Ar 4 Each independently can be phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenylnaphthyl, phenanthryl, triphenylene, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, dibenzofuranyl, or dibenzothiophenyl.
For example, ar 1 To Ar 4 Each independently may be any one selected from the following groups, but is not limited thereto:
at this time, ar 1 And Ar 2 May be identical to each other. In addition, ar 1 And Ar 2 May be different.
In addition, represents a substituent
N in the number of (a) is 0, 1 or 2 and represents a substituent
M of the number of (3) may be 0, 1 or 2. In this case, n + m may be 1,2 or 3.
Alternatively, n may be 0 or 1,m is 0 or 1, n + m is 1 or 2.
In this case, when n and m are both 1, L may be 1 And L 3 Are identical to each other, L 2 And L 4 Are identical to each other, ar 1 And Ar 3 Are mutually in phase, ar 2 And Ar 4 Are identical to each other.
In addition, R 1 And R 2 Each independently may be hydrogen or deuterium.
More specifically, R 1 And R 2 It may be all hydrogen or a mixture of hydrogen and,or both deuterium.
In addition, represents R 1 A in the number of (a) is an integer of 0 to 4-m, for example, when m is 0, a is 0, 1,2, 3 or 4,m is 1, a is 0, 1,2 or 3.
In addition, represents R 2 B of the number (b) is an integer of 0 to 6-n, for example, when n is 0, b is 0, 1,2, 3,4,5 or 6,n is 1, b is 0, 1,2, 3,4 or 5.
In addition, the above-mentioned compound may be represented by any one of the following chemical formulas 1A-1 to 1A-5, 1B-1, 1C-1 and 1C-2:
in the above chemical formulas 1A-1 to 1A-5, 1B-1, 1C-1 and 1C-2,
L、L'、L 1 to L 4 And Ar 1 To Ar 4 The same as defined in the above chemical formula 1.
On the other hand, representative examples of the compound represented by the above chemical formula 1 are as follows:
on the other hand, in the compound represented by the above chemical formula 1, when n is 0,m and 1,L is a single bond, it can be produced by the production method shown in the following reaction formula 1, as an example. The above-described manufacturing method can be further embodied in the manufacturing examples described later.
[ reaction formula 1]
In the above reaction formula 1, X is halogen, preferably bromine or chlorine, and the definitions of the other substituents are the same as those described above.
Specifically, the compound represented by the above chemical formula 1 is produced by combining the starting materials SM1 and SM2 through an amine substitution reaction. Such an amine substitution reaction is preferably carried out in the presence of a palladium catalyst and a base, and the reactive group used in the above reaction may be appropriately changed.
In addition, as an example, in the compound represented by the above chemical formula 1, when n is 0,m and 1,L is not a single bond, it can be produced by the production method shown in the following reaction formula 2. The above-described manufacturing method can be further embodied in the manufacturing examples described later.
[ reaction formula 2]
In the above reaction formula 2, X is halogen, preferably bromine or chlorine, and the definitions of the other substituents are the same as those described above.
Specifically, the compound represented by the above chemical formula 1 is manufactured by combining the starting materials SM3 and SM4 through Suzuki-Coupling reaction. Such suzuki coupling reaction is preferably carried out in the presence of a palladium catalyst and a base, and the reactive group used in the above reaction may be appropriately changed.
Otherwise, the compound represented by chemical formula 1, which is not exemplified, can be produced by appropriately changing the starting materials with reference to the above reaction formulas 1 and 2.
(organic light emitting device)
In another aspect, the present invention provides an organic light emitting device comprising the compound represented by the above chemical formula 1. As an example, the present invention provides an organic light emitting device, comprising: the organic light emitting device includes a first electrode, a second electrode disposed to face the first electrode, and 1 or more organic layers disposed between the first electrode and the second electrode, wherein 1 or more of the organic layers include a compound represented by the chemical formula 1.
The organic layer of the organic light-emitting device of the present invention may be formed of a single layer structure, but may be formed of a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic layer. However, the structure of the organic light emitting device is not limited thereto, and a smaller number of organic layers may be included.
In one embodiment, the organic layer may include a hole transport layer, a light emitting layer, and an electron injection and transport layer, and in this case, the organic layer including the compound may be a hole transport layer.
In another embodiment, the organic layer may include a hole injection layer, a hole transport layer, an electron inhibition layer, a light emitting layer, a hole blocking layer, and an electron injection and transport layer, and in this case, the organic layer including the compound may be a hole transport layer or an electron inhibition layer.
In another embodiment, the organic layer may include a hole injection layer, a hole transport layer, an electron suppression layer, a light emitting layer, a hole blocking layer, an electron injection layer, and an electron transport layer, and in this case, the organic layer including the compound may be a hole transport layer or an electron suppression layer.
The organic layer of the organic light-emitting device of the present invention may be formed of a single layer structure, but may be formed of a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including, as an organic layer, a hole injection layer and a hole transport layer between the first electrode and the light-emitting layer, and an electron transport layer and an electron injection layer between the light-emitting layer and the second electrode, in addition to the light-emitting layer. However, the structure of the organic light emitting device is not limited thereto, and a smaller number or a larger number of organic layers may be included.
In addition, the organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) in which the first electrode is an anode and the second electrode is a cathode, and the anode, 1 or more organic layers, and the cathode are sequentially stacked on the substrate. In addition, the organic light emitting device according to the present invention may be an inverted (inverted) type organic light emitting device in which the first electrode is a cathode and the second electrode is an anode, and the cathode, 1 or more organic layers, and the anode are sequentially stacked on the substrate. For example, the structure of an organic light emitting device according to an embodiment of the present invention is illustrated in fig. 1 and 2.
Fig. 1 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole transport layer 3, a light-emitting layer 4, an electron injection and transport layer 5, and a cathode 6. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above hole transport layer.
Fig. 2 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, an electron suppression layer 8, a light-emitting layer 4, a hole blocking layer 9, an electron injection and transport layer 5, and a cathode 6. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above hole injection layer, hole transport layer, or electron suppression layer.
The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that 1 or more of the above organic layers include the compound represented by the above chemical formula 1. In addition, when the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.
For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. This can be produced as follows: the organic el display device is manufactured by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate by a PVD (physical Vapor Deposition) method such as a sputtering method or an electron beam evaporation method (e-beam evaporation) method to form an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode, and then depositing a substance that can be used as a cathode on the organic layer. In addition to this method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting device.
In addition, the compound represented by the above chemical formula 1 may form an organic layer not only by a vacuum evaporation method but also by a solution coating method in manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting device can be manufactured by depositing a cathode material, an organic material layer, and an anode material on a substrate in this order (WO 2003/012890). However, the production method is not limited thereto.
In one example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.
As the anode material, a material having a large work function is generally preferable in order to smoothly inject holes into the organic layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof;metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); znO-Al or SnO 2 A combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.
In general, the cathode material is preferably a material having a small work function in order to easily inject electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; liF/Al or LiO 2 And a multilayer structure material such as Al, but not limited thereto.
The hole injection layer is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection substance: a compound having an ability to transport holes, having an effect of injecting holes from an anode, having an excellent hole injection effect for a light-emitting layer or a light-emitting material, preventing excitons generated in the light-emitting layer from migrating to an electron injection layer or an electron injection material, and having an excellent thin film-forming ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.
The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport substance is a substance that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer, and is preferably a substance having a high mobility to holes. As the hole transporting substance, a compound represented by the above chemical formula 1, an arylamine organic substance, a conductive polymer, a block copolymer in which a conjugated portion and a non-conjugated portion coexist, or the like can be used, but the hole transporting substance is not limited thereto.
The electron-suppressing layer is a layer including: and a layer which is formed on the hole transport layer, is preferably provided in contact with the light-emitting layer, and serves to prevent excessive electron transfer by adjusting hole mobility, thereby increasing the probability of hole-electron combination, and thus improving the efficiency of the organic light-emitting device. The electron-inhibiting layer contains an electron-blocking substance, and examples of such electron-blocking substances include, but are not limited to, compounds represented by the above chemical formula 1, arylamine-based organic substances, and the like.
The light-emitting substance is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and is preferably a substance having high quantum efficiency with respect to fluorescence or phosphorescence. As an example, there is an 8-hydroxyquinoline aluminum complex (Alq) 3 ) (ii) a A carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (b) is
Azole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.
The light-emitting layer may contain a host material and a dopant material as described above. The host material may further include an aromatic fused ring derivative, a heterocyclic ring-containing compound, or the like. Specifically, the aromatic condensed ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocyclic ring-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds
Pyrimidine derivatives, etc., but are not limited thereto.
As the dopant material, there are aromatic amine derivatives, styryl amine compounds, boron complexes, fluoranthene compounds, metal complexesAnd the like. Specifically, the aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, or the like having an arylamino group,
Diindenopyrene, and the like, and styrylamine compounds are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and are substituted or unsubstituted with 1 or 2 or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltrriamine, and styryltretraamine. The metal complex includes, but is not limited to, iridium complexes and platinum complexes.
The hole blocking layer is a layer including: and a layer which is formed on the light-emitting layer, preferably in contact with the light-emitting layer, and which prevents excessive hole migration by adjusting the electron mobility, thereby increasing the probability of hole-electron combination and improving the efficiency of the organic light-emitting device. The hole-blocking layer contains a hole-blocking substance, and examples of such hole-blocking substances include triazine derivatives, triazole derivatives, and the like,
Examples of the compound to which an electron-withdrawing group is introduced include, but are not limited to, oxadiazole derivatives, phenanthroline derivatives, and phosphine oxide derivatives.
The electron injection and transport layer is a layer that injects electrons from the electrode and transports the received electrons to the light-emitting layer, and functions as an electron transport layer and an electron injection layer, and is formed on the light-emitting layer or the hole blocking layer. Such an electron injecting and transporting substance is a substance that can favorably receive electrons from the cathode and transfer them to the light-emitting layer, and is suitable for a substance having a high electron mobility. As specific examples of the electron injecting and transporting substance, there are Al complexes of 8-hydroxyquinoline, al complexes containing Alq 3 Complex of (2), organic radical compound, hydroxyl groupA flavone-metal complex, a triazine derivative, and the like, but not limited thereto. Or with fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide,
Azole,
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complexes, nitrogen-containing five-membered ring derivatives, and the like are used together, but the present invention is not limited thereto.
The electron injection and transport layer may be formed as a single layer such as an electron injection layer and an electron transport layer. In this case, the electron transport layer is formed on the light-emitting layer or the hole-blocking layer, and the electron injection and transport material described above can be used as the electron transport material contained in the electron transport layer. Further, an electron injection layer is formed on the electron transport layer, and LiF, naCl, csF, or Li can be used as an electron injection substance contained in the electron injection layer 2 O, baO, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and mixtures thereof,
Azole,
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like.
Examples of the metal complex include, but are not limited to, lithium 8-quinolinolate, zinc bis (8-quinolinolate), copper bis (8-quinolinolate), manganese bis (8-quinolinolate), aluminum tris (2-methyl-8-quinolinolate), gallium tris (8-quinolinolate), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium bis (2-methyl-8-quinolinolate) chloride, gallium bis (2-methyl-8-quinolinolate) (o-cresol), aluminum bis (2-methyl-8-quinolinolate) (1-naphthol), and gallium bis (2-methyl-8-quinolinolate) (2-naphthol).
The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material used.
In addition, the compound represented by the above chemical formula 1 may be included in an organic solar cell or an organic transistor, in addition to the organic light emitting device.
The manufacture of the compound represented by the above chemical formula 1 and the organic light emitting device including the same is specifically illustrated in the following examples. However, the following examples are provided to illustrate the present invention, and the scope of the present invention is not limited thereto.
[ production example ]
Preparation example a: production of intermediate Compound A
Naphthalene-1,8-diol (20.00g, 125.00mmol) as compound substance (sub) 1 and 1-bromo-2,3-difluorobenzene (22.92g, 137.50mmol) as compound substance 2 were completely dissolved in 230mL of DMF under nitrogen atmosphere in a 500mL round-bottomed flask, and K was added 2 CO 3 (69.11g, 500.00mmol), and the mixture was stirred under heating for 5 hours. After the temperature was lowered to room temperature and the base was removed by filtration, DMF was concentrated under reduced pressure and recrystallized from 250mL of ethyl acetate to give Compound A (28.47 g, yield: 73%).
MS[M+H] + ＝314
Preparation example B: production of intermediate Compound B
An intermediate compound B was produced in the same manner as in production example a except that in production example a, the substance 3 was used instead of the substance 1.
MS[M+H] + ＝314
Production example C: production of intermediate Compound C
An intermediate compound C was produced by the same method as in production example a except that in production example a, substance 4 and substance 5 were used instead of substance 1 and substance 2, respectively.
MS[M+H] + ＝314
Production example D: production of intermediate Compound D
An intermediate compound D was produced by the same method as in production example a except that in production example a, substance 6 and substance 5 were used instead of substance 1 and substance 2, respectively.
MS[M+H] + ＝314
Preparation example E: production of intermediate Compound E
An intermediate compound E was produced by the same method as in production example a except that in production example a, substance 4 and substance 6 were used instead of substance 1 and substance 2, respectively.
MS[M+H] + ＝391
Preparation example F: production of intermediate Compound F
An intermediate compound E was produced by the same method as in production example a except that in production example a, substance 7 and substance 6 were used instead of substance 1 and substance 2, respectively.
MS[M+H] + ＝391
Production example 1: production of Compound 1
After completely dissolving Compound A (6.25g, 19.97mm. Sup. Ol) and Compound a-1 (8.72g, 21.96mmol) in 330mL of xylene in a 500mL round-bottomed flask under a nitrogen atmosphere, naOtBu (2.49g, 25.96mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.20g, 0.40mmol) was added, and the mixture was stirred under heating for 5 hours. After the temperature was lowered to room temperature and the base was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 250mL of ethyl acetate, thereby producing Compound 1 (7.74 g, yield: 62%).
MS[M+H] + ＝630
Production example 2: production of Compound 2
In a 500mL round-bottom flask under nitrogen atmosphere, after completely dissolving Compound B (6.53g, 20.86mm. Sup. Ol) and Compound a-2 (9.66g, 22.95mmol) in 320mL of xylene, naOtBu (2.61g, 27.12mmol) was added, bis (tri-tert-butylphosphine) palladium (0) (0.21g, 0.42mmol) was added, and the mixture was stirred under heating for 5 hours. After the temperature was lowered to room temperature and the base was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 310mL of ethyl acetate, thereby producing Compound 2 (9.94 g, yield: 56%).
MS[M+H] + ＝654
Production example 3: production of Compound 3
In a 500mL round-bottomed flask under nitrogen atmosphere, after completely dissolving Compound C (6.88g, 21.98mm. Sup. Ol) and Compound a-3 (10.18g, 24.18mmol) in 320mL of xylene, naOtBu (2.75g, 28.58mmol) was added, bis (tri-tert-butylphosphine) palladium (0) (0.22g, 0.44mmol) was added, and the mixture was stirred under heating for 6 hours. After the temperature was lowered to room temperature and the base was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 340mL of ethyl acetate, thereby producing Compound 3 (8.81 g, yield: 61%).
MS[M+H] + ＝654
Production example 4: production of Compound 4
In a 500mL round-bottom flask under nitrogen atmosphere, after completely dissolving compound D (7.13g, 22.78mm ol) and compound a-4 (10.30g, 25.06mmol) in 320mL of xylene, naOtBu (2.85g, 29.61mmol) was added, bis (tri-tert-butylphosphine) palladium (0) (0.23g, 0.46mmol) was added, and the mixture was stirred under heating for 7 hours. After the temperature was lowered to room temperature and the base was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 270mL of ethyl acetate, thereby producing Compound 4 (7.95 g, yield: 54%).
MS[M+H] + ＝644
Production example 5: production of Compound 5
In a 500mL round-bottom flask under nitrogen, after completely dissolving Compound A (6.13g, 19.58mmol) and Compound a-5 (7.44g, 21.54mmol) in 240mL of tetrahydrofuran, 2M aqueous potassium carbonate (120 mL) was added, and after adding tetrakis (triphenylphosphine) palladium (0.68g, 0.59mmol), stirring was carried out under heating for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the residue was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 350mL of ethyl acetate to obtain Compound 5 (9.26g, 75%).
MS[M+H] + ＝630
Production example 6: production of Compound 6
After completely dissolving compound B (6.55g, 20.93mmol) and compound a-6 (9.09g, 23.02mmol) in 240mL of tetrahydrofuran in a 500mL round-bottom flask under a nitrogen atmosphere, a 2M aqueous potassium carbonate solution (120 mL) was added, and after adding tetrakis (triphenylphosphine) palladium (0.73g, 0.63mmol), the mixture was stirred with heating for 7 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the residue was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 340mL of ethyl acetate to obtain Compound 6 (8.88g, 62%).
MS[M+H] + ＝680
Production example 7: production of Compound 7
After completely dissolving compound C (6.49g, 20.73mmol) and compound a-7 (7.87g, 22.81mmol) in 240mL of tetrahydrofuran in a 500mL round-bottomed flask under a nitrogen atmosphere, a 2M aqueous potassium carbonate solution (120 mL) was added, and after adding tetrakis (triphenylphosphine) palladium (0.72g, 0.62mmol), the mixture was stirred under heating for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the residue was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 310mL of ethyl acetate to obtain Compound 7 (7.93g, 61%).
MS[M+H] + ＝630
Production example 8: production of Compound 8
After completely dissolving compound D (5.98g, 19.11mmol) and compound a-8 (8.85g, 21.02mmol) in 240mL of tetrahydrofuran in a 500mL round-bottomed flask under a nitrogen atmosphere, a 2M aqueous potassium carbonate solution (120 mL) was added, and after adding tetrakis (triphenylphosphine) palladium (0.66g, 0.57mmol), the mixture was stirred under heating for 5 hours. After the temperature was lowered to room temperature and the aqueous layer was removed and dried over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 420mL of ethyl acetate to obtain Compound 8 (10.07g, 75%).
MS[M+H] + ＝706
Production example 9: production of Compound 9
After completely dissolving Compound B (6.48g, 20.70mm. Sup. Ol) and Compound a-9 (11.36g, 22.77mmol) in 300mL of xylene in a 500mL round-bottomed flask under a nitrogen atmosphere, naOtBu (2.59g, 26.91mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.21g, 0.41mmol) was added, and the mixture was stirred under heating for 5 hours. After the temperature was lowered to room temperature and the base was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 360mL of ethyl acetate, thereby producing Compound 9 (9.11 g, yield: 60%).
MS[M+H] + ＝732
Production example 10: production of Compound 10
After completely dissolving compound B (7.34g, 23.45mm ol) and compound a-10 (10.09g, 25.80mmol) in 300mL of xylene in a 500mL round-bottomed flask under a nitrogen atmosphere, naOtBu (2.93g, 30.49mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.24g, 0.47mmol) was added, and the mixture was stirred under heating for 5 hours. After the temperature was lowered to room temperature and the base was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 280mL of ethyl acetate, thereby producing compound 10 (7.87 g, yield: 54%).
MS[M+H] + ＝624
Production example 11: production of Compound 11
After completely dissolving compound E (5.26g, 16.81mm. Sup. Ol) and compound a-11 (7.74g, 35.29mmol) in 300mL of xylene in a 500mL round-bottomed flask under a nitrogen atmosphere, naOtBu (4.04g, 42.01mmol) was added, bis (tri-tert-butylphosphine) palladium (0) (0.34g, 0.67mmol) was added, and the mixture was stirred under heating for 4 hours. After the temperature was decreased to normal temperature and the base was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 280mL of ethyl acetate to produce compound 11 (7.13 g, yield: 63%).
MS[M+H] + ＝669
Production example 12: production of Compound 12
In a 500mL round-bottomed flask under nitrogen atmosphere, after completely dissolving Compound F (5.55g, 17.73mm ol) and Compound a-12 (11.01g, 37.24mmol) in 300mL of xylene, naOtBu (4.26g, 44.33mmol) was added, bis (tri-tert-butylphosphine) palladium (0) (0.36g, 0.71mmol) was added, and the mixture was stirred under heating for 7 hours. After the temperature was lowered to room temperature and the base was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 250mL of ethyl acetate, thereby producing compound 12 (8.36 g, yield: 57%).
MS[M+H] + ＝821
Production example 13: production of Compound 13
After completely dissolving compound E (5.11g, 13.04mmol) and compound a-13 (8.29g, 28.68mmol) in 240mL of tetrahydrofuran in a 500mL round-bottomed flask under a nitrogen atmosphere, a 2M aqueous potassium carbonate solution (120 mL) was added, tetrakis (triphenylphosphine) palladium (0.90g, 0.78mmol) was added, and the mixture was stirred under heating for 6 hours. The temperature was lowered to normal temperature, the aqueous layer was removed, and the residue was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 340mL of ethyl acetate to obtain Compound 13 (7.44g, 79%).
MS[M+H] + ＝721
Examples 1 to 1
Indium Tin Oxide (ITO) and a process for producing the same
The glass substrate coated with a thin film of (3) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. In this case, the detergent was prepared by Fischer co, and the distilled water was filtered twice by a Filter (Filter) manufactured by Millipore co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone, or methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.
On the ITO transparent electrode as the anode thus prepared, the following compound HI1 and the compound of the following compound HI2 were mixed at a ratio of 98 (molar ratio)
The hole injection layer is formed by thermal vacuum deposition. On the hole injection layer, compound 4 produced in production example 4 was added
The hole transport layer is formed by vacuum evaporation. Then, on the hole transport layer, the film thickness
The compound of EB1 was vacuum-evaporated to form an electron suppression layer.
Next, the electron inhibiting layer is formed on the substrate to a film thickness
A compound represented by the following chemical formula BHThe compound represented by the following chemical formula BD and the compound were vacuum-evaporated at a weight ratio of 25 to form a light-emitting layer.
On the light-emitting layer, the thickness of the film
The compound represented by chemical formula HB1 is vacuum-evaporated to form a hole blocking layer. Next, on the hole blocking layer, a compound represented by the following chemical formula ET1 and a compound represented by the following chemical formula LiQ were vacuum-evaporated at a weight ratio of 1:1 to form a hole blocking layer
The thickness of (a) forms an electron injection and transport layer. On the above electron injection and transport layer, lithium fluoride (LiF) is sequentially added to
Thickness of aluminum and
the thickness of (3) is evaporated to form a cathode.
In the above process, the evaporation speed of the organic material is maintained
Second, maintenance of lithium fluoride at the cathode
Vapor deposition rate per second, aluminum maintenance
A vapor deposition rate per second, and a degree of vacuum maintained at 2X 10 during vapor deposition -7 ～5×10 -6 And supporting to thereby fabricate an organic light emitting device.
Examples 1-2 to examples 1-5
An organic light-emitting device was produced in the same manner as in example 1-1 above, except that the compound described in table 1 below was used instead of the compound of production example 1. At this time, the structures of the compounds used in the above examples are arranged as follows.
Comparative examples 1-1 to 1-3
An organic light-emitting device was produced in the same manner as in example 1-1 above, except that the compound described in table 1 below was used instead of the compound of production example 1. In this case, the structures of the compounds HT1, HT2 and HT3 used in Table 1 above are shown below.
Experimental example 1
When a current was applied to the organic light emitting devices manufactured in the above examples and comparative examples, the voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in table 1 below. T95 refers to the time required for the luminance to decrease from the initial luminance (1600 nits) to 95%.
[ Table 1]
As shown in table 1 above, the organic light emitting devices of the examples using the compound represented by chemical formula 1 as a hole transport layer material showed excellent characteristics in terms of driving voltage, light emitting efficiency, and lifetime, as compared to the organic light emitting devices of the comparative examples.
Specifically, it was confirmed that the organic light emitting device of the above embodiment has a lower driving voltage while showing improved efficiency and a significantly long life as compared to the organic light emitting devices of comparative examples 1-1 to 1-3, which respectively employ HT1, HT2 and HT3 substances having a diamine structure and conventionally frequently used as hole transport layer substances.
Example 2-1 to example 2-7
An organic light-emitting device was produced in the same manner as in example 1-1, except that in example 1-1, the HI compound was used as the hole transport layer instead of compound 4 produced in production example 4, and that as the electron inhibiting layer, a compound described in table 2 below was used instead of compound EB 1. At this time, the structures of the compounds used in the above examples are arranged as follows.
Comparative examples 2-1 and 2-2
An organic light-emitting device was produced in the same manner as in example 2-1 above, except that the compound described in table 2 below was used instead of the compound of example 2-1. In this case, the structures of the compounds EB2 and EB3 used in table 2 below are shown below.
Experimental example 2
When a current was applied to the organic light emitting devices manufactured in the above examples and comparative examples, the voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in table 2 below. T95 refers to the time required for the luminance to decrease from the initial luminance (1600 nits) to 95%.
[ Table 2]
As shown in table 2, the organic light emitting devices of the examples using the compound represented by chemical formula 1 as the electron inhibiting layer material showed excellent characteristics in driving voltage, light emitting efficiency, and lifetime, as compared to the organic light emitting devices of the comparative examples
Specifically, it was confirmed that the organic light emitting device of the above-described embodiment has a lower driving voltage, while exhibiting improved efficiency and a significantly long lifetime, as compared to the organic light emitting devices of comparative examples 2-1 to 2-2, which respectively employ EB2 and EB3 having a diamine structure and conventionally frequently used as electron inhibiting layer materials.
[ description of symbols ]
1: substrate 2: anode
3: hole transport layer 4: luminescent layer
5: electron injection and transport layer 6: cathode electrode
7: hole injection layer 8: electron inhibiting layer
9: a hole blocking layer.
Claims (12)
1. A compound represented by the following chemical formula 1:
chemical formula 1
In the chemical formula 1, the first and second organic solvents,
l, L' and L 1 To L 4 Each independently is a single bond, or substituted or unsubstituted C 6-60 An arylene group, a cyclic or cyclic alkylene group,
Ar 1 to Ar 4 Each independently substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C containing 1 or more heteroatoms of N, O and S 2-60 (ii) a heteroaryl group, wherein,
R 1 and R 2 Each independently hydrogen, deuterium, substituted or unsubstituted C 1-60 Alkyl, or substituted or unsubstituted C 6-60 An aryl group, a heteroaryl group,
n and m are each independently an integer of 0 to 2,
however, n + m is 1 to 3,
a is an integer of 0 to 4-m,
b is an integer of 0 to 6-n.
2. The compound according to claim 1, wherein the compound is represented by any one of the following chemical formulae 1A to 1C:
chemical formula 1A
Chemical formula 1B
Chemical formula 1C
In the chemical formulas 1A to 1C,
L、L'、L 1 to L 4 、Ar 1 To Ar 4 、R 1 、R 2 N, m, a and b are as defined in claim 1.
3. The compound of claim 1, wherein L and L' are each independently a single bond, or are selected from any one of the following:
4. the compound of claim 1, wherein L 1 To L 4 Each independently a single bond, phenylene, biphenyldiyl, or naphthylene.
5. The compound of claim 1, wherein Ar 1 To Ar 4 Each independently is phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenylnaphthyl, phenanthryl, triphenylene, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, dibenzofuranyl, or dibenzothiophenyl.
6. The compound of claim 5, wherein Ar 1 To Ar 4 Each independently is any one selected from the following:
7. the compound of claim 1, wherein R 1 And R 2 Each independently hydrogen or deuterium.
8. The compound of claim 1, wherein n + m is 1 or 2.
9. The compound according to claim 1, wherein the compound is represented by any one of the following chemical formulae 1A-1 to 1A-5, 1B-1, 1C-1 and 1C-2:
in the chemical formulas 1A-1 to 1A-5, 1B-1, 1C-1 and 1C-2,
L、L'、L 1 to L 4 And Ar 1 To Ar 4 As defined in claim 1.
10. The compound of claim 1, wherein the compound is any one selected from the group consisting of:
11. an organic light emitting device, comprising: a first electrode, a second electrode provided so as to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the compound according to any one of claims 1 to 10.
12. The organic light emitting device of claim 11, wherein the organic layer comprising the compound is a hole transport layer or an electron suppression layer.
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| PCT/KR2021/006623 WO2022050533A1 (en) | 2020-09-07 | 2021-05-27 | Novel compound and organic light-emitting device using same |
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| KR20170047472A (en) * | 2015-10-22 | 2017-05-08 | 삼성디스플레이 주식회사 | Compound and Organic light emitting device comprising same |
| KR20170067643A (en) * | 2015-12-08 | 2017-06-16 | 롬엔드하스전자재료코리아유한회사 | Organic electroluminescent compound and organic electroluminescent device comprising the same |
| KR20170074649A (en) * | 2015-12-22 | 2017-06-30 | 주식회사 두산 | Organic compounds and organic electro luminescence device comprising the same |
| JP6446099B1 (en) * | 2017-07-18 | 2018-12-26 | 彩豐精技股▲分▼有限公司 | Novel compounds and organic electronic devices containing the same |
| KR20190088909A (en) * | 2018-01-19 | 2019-07-29 | 롬엔드하스전자재료코리아유한회사 | Organic electroluminescent compound and organic electroluminescent device comprising the same |
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| KR100430549B1 (en) | 1999-01-27 | 2004-05-10 | 주식회사 엘지화학 | New organomattalic complex molecule for the fabrication of organic light emitting diodes |
| KR20210152919A (en) * | 2020-06-09 | 2021-12-16 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| CN112521343B (en) * | 2020-11-23 | 2022-10-14 | 北京八亿时空液晶科技股份有限公司 | Organic electroluminescent material and device thereof |
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| KR20170047472A (en) * | 2015-10-22 | 2017-05-08 | 삼성디스플레이 주식회사 | Compound and Organic light emitting device comprising same |
| KR20170067643A (en) * | 2015-12-08 | 2017-06-16 | 롬엔드하스전자재료코리아유한회사 | Organic electroluminescent compound and organic electroluminescent device comprising the same |
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| JP6446099B1 (en) * | 2017-07-18 | 2018-12-26 | 彩豐精技股▲分▼有限公司 | Novel compounds and organic electronic devices containing the same |
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